Regiochemistry of epoxide ring opening in methyl 2,3-anhydro-4-azido-4- deoxy-α- and β-L-lyxopyranosides

Carbohydrate Research

Volumn 340, Issue 11, 2005, Pages 1866-1871

  Popsavin, Velimir ^a   Benedeković, Goran ^a   Popsavin, Mirjana ^a   Srećo, Bojana ^a   Djoković, Dejan ^b  

^a UNIVERSITY OF NOVI SAD   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

2,3 Anhydro lyxopyranosides; 2,3 Anhydro ribopyranosides; Azido sugars; Epoxide ring opening; Regioselectivity

Indexed keywords

CHEMICAL ANALYSIS; NEGATIVE IONS; NITROGEN COMPOUNDS; RING OPENING POLYMERIZATION;

CHEMICAL BEHAVIOR; EPOXIDE RING OPENING; REGIOCHEMISTRY; SOLVOLYTIC CONDITIONS;

ALCOHOLS;

ARABINOSE; AZIDE; EPOXIDE; METHYL 2,3 ANHYDRO 4 O METHANESULFONYL ALPHA DEXTRO RIBOPYRANOSIDE; PYRANOSIDE; UNCLASSIFIED DRUG;

ARTICLE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; SOLVOLYSIS; STEREOCHEMISTRY;

EID: 22044453656     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2005.06.006     Document Type: Article

References (17)

1. For reviews, see: N.R. Williams Adv. Carbohydr. Chem. Biochem. 25 1970 109 180
2. M. Černy Adv. Carbohydr. Chem. Biochem. 58 2003 121 198
3. P.K. Vasudeva, and M. Nagarajan Tetrahedron 52 1996 5607 5616
4. P.K. Vasudeva, and M. Nagarajan Tetrahedron 52 1996 1747 1766
5. F. Calvani, P. Crotti, C. Gardelli, and M. Pinechi Tetrahedron 50 1994 12999 13022
6. M.V. Rao, and M. Nagarajan J. Org. Chem. 53 1988 1184 1191
7. H. Hashimoto, F. Chiba, K. Araki, and J. Yoshimura Carbohydr. Res. 72 1979 261 266
8. M. Mastihubová, and P. Biely Tetrahedron Lett. 42 2001 9065 9067
9. V. Popsavin, G. Benedeković, M. Popsavin, V. Divjaković, and T. Ambruster Tetrahedron 60 2004 5225 5235
10. M. Kiso, and A. Hasegawa Carbohydr. Res. 52 1976 95 102
11. H.B. Wood, and H.G. Fletcher Jr. J. Am. Chem. Soc. 80 1958 5242 5246
12. A. Banaszek, and B. Janisz Tetrahedron: Asymmetry 11 2000 4693 4700
13. A.J. Dick, and J.K.N. Jones Can. J. Chem. 45 1967 2879 2885
14. J.G. Buchanan, and H.Z. Sable B.S. Thyagarajan Selective Organic Transformations Vol. 2 1972 Wiley-Interscience New York 1 95
15. R. Allerton, and W.G. Overend J. Chem. Soc. 1954 3629 3632
16. A.J. Dick, and J.K.N. Jones Can. J. Chem. 44 1966 79 87
17. H. Yuasa, and H. Hashimoto J. Am. Chem. Soc. 121 1999 5089 5090